- Reaction of trifluoro-N-(oxo-λ4-sulfanylidene)methanesulfonamide with pyrazolidin-3-ones
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Trifluoro-N-(oxo-λ4-sulfanylidene)methanesulfonamide reacted with 1-phenylpyrazolidin-3-one and 4-methyl-1-phenylpyrazolidin-3-one to give 1-phenyl-1,2-dihydro-3H-pyrazol-3-ones. A probable oxidation mechanism was proposed.
- Shainyan,Tolstikova
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- Decomposition of N-cyclopropyl-N-nitrosourea in the presence of reducing agents as a new way of generating the cyclopropyl radical
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A new way of generating cyclopropyl radicals in the base-catalyzed decomposition of N-cyclopropyl-N-nitrosourea in the presence of organic reducing agents (1-phenylpyrazolidin-3-one and 4-methoxyphenol) was developed. The cyclopropyl radical generated und
- Tomilov,Kostyuchenko,Okonnishnikova,Klimenko,Shulishov
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- Solvent-free and montmorillonite K10-catalyzed domino reactions for the synthesis of pyrazoles with alkynylester as a dual synthon
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A highly regioselective, solvent-free and montmorillonite K10 clay-catalyzed domino process with an unprecedented ring-closing C-C bond-formation reaction is described for the synthesis of a new class of 1,3,4-trisubstituted and 1,4-disubstituted pyrazole
- Annes, Sesuraj Babiola,Ramesh, Subburethinam,Saritha, Rajendhiran,Shankar, Bhaskaran,Subramanian, Saravanan
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supporting information
p. 2388 - 2393
(2020/05/13)
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- ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES
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A compound having a structure of the formula Ir(LA)(LB), in which LA is a bidentate, tridentate, tetradentate, pentadentate, or hexadentate ligand and LB is a monodentate, bidentate, tridentate, or tetradentate ligand, or not present, and where the total denticity of LA plus LB is 6, and LA includes at least one structure of Formula I: is disclosed as a useful phosphorescent emitter compound.
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Paragraph 0196
(2019/02/25)
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- Amide compound and application thereof
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The invention provides an amide compound and application thereof. Compared with compounds in the prior art, the compound disclosed by the invention has the advantage that the bactericidal activity isobviously improved. The invention is expected to develop a bactericide which is in novel structure and is used for controlling diseases in agriculture, forestry or sanitation.
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Paragraph 0144; 0149-0151
(2018/09/28)
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- Synthesis, fungicidal activity, structure-activity relationship and density functional theory studies of novel oxime ether derivatives containing 1-aryl-3-oxypyrazoles
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A series of 16 oxime ether derivatives containing 1-aryl-3-oxypyrazoles were synthesised, and the structure of one of them, (E)-methyl 2-(2-({(1-(4-chlorophenyl)-1H-pyrazol-3-yl)-oxy}methyl)phenyl)-2-(methoxyimino)acetate was determined by X-ray diffraction crystallography. Preliminary bioassays indicated that some of these compounds exhibited very good fungicidal activities against Rhizoctonia solani, especially the ester 2-(2-({(1-(4-chlorophenyl)-1H-pyrazol-3-yl)-oxy}methyl)phenyl)-2-(methoxyimino)acetate, which displayed greater activity than control compound pyraclostrobin at a dosage of 0.1 μg mL-1. The relationship between structure and fungicidal activity was discussed. Density functional theory studies of the 3-methyl heterocyclic ester and the 4-chorophenyl heterocyclic N-methylamide were carried out and the results discussed in terms of the wide difference in fungicidal activity shown by each compound.
- Lv, Kunzhi,Liu, Yuanyuan,Li, Yi,Xu, Guanghui,Pan, Xuechun,Li, Fangshi,Chen, Kai,Huang, Bin,Yang, Yaping
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p. 594 - 600
(2015/11/27)
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- Synthesis and fungicidal activity of novel chloro-containing 1-Aryl-3-oxypyrazoles with an oximino ester or oximino amide moiety
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Six novel chloro-containing 1-aryl-3-oxypyrazoles TMa-TMf with an oximino ester or an oximino amide moiety were prepared by the reaction of 1-aryl-1H-pyrazol-3-ols with benzyl bromide. Their structures were characterized by 1H-NMR, 13C-NMR, IR, MS, and elemental analysis. A preliminary in vitro bioassay indicated that compounds TMa, TMe and TMf displayed excellent fungicidal activity against Rhizoctonia solani and could be used as potential lead compounds for further development of novel fungicides.
- Liu, Yuanyuan,Li, Yi,Chen, Nanqing,Lv, Kunzhi,Zhou, Chao,Xiong, Xiaohui,Li, Fangshi
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p. 8140 - 8150
(2014/07/08)
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- TETRAZOLINONE COMPOUNDS AND ITS USE AS PESTICIDES
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The present invention provides a compound having an excellent efficacy for controlling pests. A tetrazolinone compound of a formula (1): [wherein R1 represents an C6-C16 aryl group, an C1-C12 alkyl group, or a C3-C12 cycloalkyl group, etc., which each optionally be substituted; R2, R3, R4 and R5 represent independently of each other a hydrogen atom, a halogen atom or an C1-C3 alkyl group, etc.; R6 represents an C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogen atom, a C1-C6 haloalkyl group, an C2-C6 alkenyl group, an C1-C6 alkoxy group, or a C1-C6 haloalkoxy group, etc.; R7, R8 and R9 represent independently of each other a hydrogen atom, a halogen atom, or an C1-C4 alkyl group, etc.; X represents an oxygen atom or a sulfur atom; and R10 represents an C1-C6 alkyl group, etc.] shows an excellent controlling efficacy on pests.
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Page/Page column 955
(2013/11/18)
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- DMF-catalyzed direct and regioselective C-H functionalization: Electrophilic/nucleophilic 4-halogenation of 3-oxypyrazoles
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A novel, straightforward, and highly regioselective 4-chlorination of 3-oxypyrazole derivatives in boiling thionyl chloride (SOCl2) in the presence of catalytic N,N-dimethylformamide (DMF) has been developed. This reaction likely proceeds through a DMF-catalyzed electrophilic/nucleophilic chlorination mechanism and involves electrophilic attack by SOCl2 and nucleophilic substitution by Cl- as the key steps. Based on this mechanism, the corresponding 4-bromination and 4-iodination of 3-oxypyrazoles have also been achieved in good yield by adding Br- and I -, respectively, to the reaction system. This halogenation method enables quick access to many original 4-halo-3-oxypyrazole series. A novel DMF-catalyzed electrophilic/nucleophilic 4-halogenation of 3-oxypyrazole derivatives has been developed. This halogenation procedure provides quick access to many novel 4-halo-3-oxypyrazole series.
- Liu, Yuanyuan,He, Guangke,Chen, Kai,Jin, Yin,Li, Yufeng,Zhu, Hongjun
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p. 5323 - 5330
(2011/11/13)
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- Alkoxypyrazoles and the process for their preparation
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The present invention relates to a process for the preparation of alkoxypyrazoles and new alkoxypyrazole compounds.
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Page/Page column 15; 17
(2010/03/02)
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- 5-Iodo-3-ethoxypyrazoles: An entry point to new chemical entities
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Our program, which has focused on the preparation of new pyrazole derivatives, has led us to report here an original and simplified preparation of ethyl 3-ethoxy-lW-pyrazole-4-carboxylate. This is based on the reaction of hydrazine monohydrochloride and diethyl 2-(ethoxymethylene)malonate. Further transformations of this key compound allowed the preparation of the two possible iodinated isomers, namely, 3-ethoxy-4-iodo- and 3-ethoxy-5-iodo-1H-pyrazole. These compounds have opened the way to a quick access to many original pyrazole series. As an illustration, we report here on the selectivity of N-arylation, by using the Lam and Cham method, the C4- and C5-arylation of some of these 3-ethoxy-pyrazole derivatives by using the Suzuki-Miyaura reaction, and C5-benzylation reactions by means of the Negishi reaction. This was followed by hydrolysis of the ethoxy group, which led to the corresponding pyrazol-3-one derivatives. As a conclusion of this work, we conducted an investigation into the regiochemistry of the condensation between diethyl 2-(ethoxymethylene) malonate and the hydrochloride salts of methyl, benzyl, or phenyl hydrazine.
- Guillou, Sandrine,Janin, Yves L.
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experimental part
p. 4669 - 4677
(2010/08/06)
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- Synthesis, crystal structure and fungicidal activities of new type oxazolidinone-based strobilurin analogues
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A series of oxazolidinone-based strobilurin analogues were efficiently synthesized by the reaction of 3-(2-bromomethylphenyl) oxazolidin-2-one with 1-substituted phenyl-2H-pyrazolin-3-one. Their structures were confirmed and characterized by 1H-NMR, 13C-NMR, elemental analysis, and mass spectroscopy. In addition, the crystal structure of the target compound 3-(2-((1-phenyl-2H-pyrazol-3-yloxy)methyl)phenyl) oxazolidin-2-one was determined by single crystal X-ray diffraction. The bioassay results of these compounds indicated that some of the oxazolidin-2-one derivatives containing N-substituted phenyl 2H-pyrazol ring exhibited potential in vivo fungicidal activities against M. grisea at the dosage of 1 g L-1.
- Li, Yuhao,Liu, Rui,Yan, Zhangwei,Zhang, Xiangning,Zhu, Hongjun
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p. 3341 - 3347
(2012/05/05)
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- Pyrazolyl-substituted polyconjugated molecules for optoelectronic applications
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Pyrazolyl-substituted diethylene derivative and its analogue containing additional cyano groups were synthesized and investigated as potential multifunctional materials for organic light emitting diodes. The influence of the electron affinitive cyano groups on the ionization potential (Ip) of the films as well as on the photoluminescence (PL) spectrum, PL quantum yield (η) and PL decay time of the dilute solutions and thin films of the pyrazole derivatives was studied. PL measurements revealed that highly luminescent (η?=?0.88) cyano-free pyrazole derivative in solution became non-emissive (η?=?0.01) by attaching cyano groups as a result of these groups-induced torsional deactivation. However in the solid state, the steric and electrostatic effects of the bulky and polar cyano groups prevented tight packing of the pyrazole derivative molecules, thus significantly reducing migration-induced quenching of the excitons at the defects. Incorporation of the cyano groups resulted in the two-fold enhancement of the PL quantum yield in the film of the pyrazole derivative as compared to that of the cyano-free film. The Ip of 5.90?eV estimated for the cyano groups-containing compound was found to be higher as compared to the Ip of 5.46?eV for cyano-free analogue, what in conjunction with the PL data for the films indicates increased electron affinity in the pyrazole derivative with additional cyano groups.
- Arba?iauskiene,Kazlauskas,Miasojedovas,Jur?enas,Jankauskas,Holzer,Getautis,?a?kus
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scheme or table
p. 79 - 85
(2010/11/16)
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- Pd-catalyzed cross-coupling reactions of halogenated 1-phenylpyrazol-3-ols and related triflates
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1-Phenyl-1H-pyrazol-3-ol was used as a versatile synthon for the preparation of various 1-phenyl-1H-pyrazole derivatives substituted at C-3 and C-4 of the pyrazole nucleus and at the phenyl ring para-position. Treatment of 1-phenyl-1H-pyrazol-3-ol with tr
- Arba?iauskiene, Egle,Vilkauskaite, Gyte,Eller, Gernot A.,Holzer, Wolfgang,?a?kus, Algirdas
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scheme or table
p. 7817 - 7824
(2009/12/26)
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- Synthesis and biological evaluation of new phenidone analogues as potential dual cyclooxygenase (COX-1 and COX-2) and human lipoxygenase (5-LOX) inhibitors
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A new series of potential human 5-LOX inhibitors structurally related to the 1-phenyl-3-pyrazolidinone (phenidone, 2) has been synthesized and the activity against COX-1, COX-2, and human 5-LOX enzymes has been evaluated. In contrast with literature data, we observed that phenidone resulted to be inactive against human 5-LOX, while retains its activity against cyclooxygenases in a micromolar range. The present results suggest that the substitution of the amino function at the 4-position is detrimental in terms of activity toward COX-1 and COX-2, while the presence of a double bond at the 4,5-position does not alter the biological profile against COX. The absence of activity vs. human 5-LOX strongly suggests a re-consideration of phenidone and its analogs as 5-LOX inhibitors in humans.
- Cusan, Claudia,Spalluto, Giampiero,Prato, Maurizio,Adams, Michael,Bodensieck, Antje,Bauer, Rudolf,Tubaro, Aurelia,Bernardi, Paolo,Da Ros, Tatiana
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- Electrochemical Oxidation of 1-Phenylpyrazolidin-3-ones. Part 2. 1-Aryl-4,4-dimethylpyrazolidin-3-ones
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The electrochemical oxidation of 1-phenyl- and 1-(2,4-dimethylphenyl)-4,4-dimethylpyrazolidin-3-one has been studied.Nucleophilic attack on a 3-oxopyrazolidin-5-yl cation appears to be common route to all the products which have been characterised.
- Bellamy, Anthony J.,Innes, David I.,Hillson, Peter J.
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p. 175 - 178
(2007/10/02)
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- Electrochemical Oxidation of 1-Phenylpyrazolidin-3-ones. Part 3. Reaction Mechanism
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A cyclic voltammetric study of 1-phenylpyrazolidin-3-one and some typical substituted analogues has shown that the chemical step following the initial electron transfer involves deprotonation of the cation-radical at position 2 (NH).In the abscence of added base and at substrate concentration >2mM, the substrate itself deprotonates the cation-radical.In the presence of basic chloride ions oxidation occurs via the conjugate base of 1-phenylpyrazolidin-3-one.The lifetime of the cation-radical is relatively insensitive to the nature of the substituents at C(4) and C(5), but is increased markedly by substitution at N(2).
- Bellamy, Anthony J.,Innes, David I.,Hillson, Peter J.
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p. 179 - 182
(2007/10/02)
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- Electrochemical Oxidation of 1-Phenylpyrazolidin-3-ones. Part 1. 4- and 5-Substituted 1-Phenylpyrazolidin-3-ones
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The electrochemical oxidation of 4-methyl-, 5-phenyl-, and 4-hydroxymethyl-4-methyl-1-phenylpyrazolidin-3-one in acetonitrile has been studied.All three systems behave in a manner similar to that of the parent 1-phenylpyrazolidin-3-one, the major reaction
- Bellamy, Anthony J.,Innes, David I.,Hillson, Peter J.
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p. 1599 - 1604
(2007/10/02)
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